I’ve Had 18 Roles in My 36-Year Career. Here’s How I Know When to Go Job Hunting.

I’ve Had 18 Roles in My 36-Year Career. Here’s How I Know When to Go Job Hunting.

By Art Wittmann, editor of Brainyard
7-minute read

In short:

  • It’s not hard to optimize your career for earnings. Balancing mastery, work/life ratio and cultural fit is a lot more nuanced.
  • Bad bosses make the “Should I stay or should I go?” decision a lot simpler.
  • If indecision’s bugging you, we have five questions to add clarity.


One of the best jobs I’ve ever had was at the University of Wisconsin, Madison. It was also one of the worst jobs I’ve ever had. On the plus side, I helped students get educated and worked alongside some of the smartest people I’ve ever met. On the downside, there was a lot of pressure in the ’80s and ’90s to contain the cost of the state’s huge -- more than 180,000 students on 26 campuses -- post-secondary education system.

Annual raise time was excruciating. Yearly raise pools were typically around 2% of salaries at a time when inflation hovered at 5%. The difference between star performers and laggards was typically 1%. Meanwhile, campus leaders argued that if you worked in IT or a top research area, you were in demand and should get more cash. That didn’t sit well with the liberal arts staff, so bad blood spilled over pennies while everyone lost ground to inflation.

People who loved their jobs despite it all often had side gigs. It was the only way to stay ahead.

I worked there for five years as a student and nine years as academic staff. Finally, it just wasn’t cost-effective to remain. I could more than double my salary by moving to a private company, so I did.

At the time, people were surprised. After almost 15 years, I was established at the University and could have moved around within the institution, as was common then. Friends who worked for IBM and GM often made lateral moves that led to vertical progress. Midwesterners might have five to 10 roles throughout their careers, but usually they were within one or two firms.

Company hopping? That was for the coastal elites.

Deciding to change jobs can be confusing. The questions below will help you determine when it's time to go.

Since my time at the UW, I’ve worked for two startups, three large companies and one private equity (PE)-held company (they’re unique). I’ve gone through two acquisitions, been laid off once and worked for myself twice for a total of about nine years. I’ve managed brands and teams. I’ve started some products and shut down others. You’d think I’d have insights about when to leave a job and when to stay.

You’d think so, but the fact is, I don’t have any pithy advice on what makes for a great work environment and an equally good career strategy. You can easily find advice on how to maximize your earnings, which often amounts to "find a new job every two years."

If money is your only driving factor, that’s all the advice you need. But for most professionals, conventional wisdom is that it takes nine months to a year to really know your job, your boss and your constituents and produce at top efficiency. To my mind, being comfortable with a two-years-and-out strategy means being comfortable with rarely producing at your full skill level and capacity. At some point, pride in your work and confidence in your performance is likely to be at least as important as your BMW or Hamptons aspirations.


If money is your only driving factor, that’s all the advice you need. But at some point, pride in your work and confidence in your performance is likely to be at least as important.  


 Nonetheless, few people will work for just one or two companies in their lifetimes. That’s certainly true for those entering the workforce now. So it’s important to have a matrix to help decide when it’s time to start sending out resumes.

Here’s some food for thought.


5 questions to determine whether it's time for a new job


1. What’s your comfort level? 

I recommend finding a job in which you feel challenged, but not drowned; valued, but not abused; and confident, but not bored. These factors are the most important because they are about you -- not the company nor your boss, but how you feel about your workday when you get up in the morning. 

🌱 I recommend finding a job in which you feel challenged, but not drowned; valued, but not abused; and confident, but not bored.

We all like new challenges, but not many of us like facing Mt. Everest every day, even with a great climbing team. I start questioning when the challenges lead to an unhealthy lifestyle -- perhaps your blood pressure starts acting up, as mine did in my late 30s, or work steals the time you need for family, friends, exercise or other endeavors that are dear to you, whether charitable causes or your painting passion. 

Mastery is important. And yet, at some point in every job, you’re likely to feel utterly clueless. You’ll feel less-than-challenged at other times. If these are rare occasions, you’re doing fine. For myself, I like to be just slightly uncomfortable with my job -- not 100% sure how to do everything I’m supposed to do. It means I’m still learning, and that’s good for me. 


2. Do you like your boss? And is your boss empowered to take care of you? 

Good bosses who help you achieve mastery, get you interesting assignments, build great teams that leverage your skills and congratulate you when you do well are a blessing of the first order. Great bosses needn’t be more skilled at your job than you are. Nor do they need to be super smart or incredibly eloquent. But they do need to appreciate and like you, and they need to be adept at managing within the structure of the company. 

🌱 Great bosses needn’t be more skilled than you are. But they do need to appreciate and like you, and they need to be adept at managing within the structure of the company.

It’s been suggested that the term “manager” should be retired in favor of “coach” or “leader” or something similar, and I can see the merit of that. It’s good to have a boss who can lead, but it’s also good to have a boss who listens and then manages through the organization to implement great ideas, no matter where they originated. Coaches and leaders can’t or won’t always do that. 

Your boss doesn’t need to be your drinking buddy, vote like you or remember that you hate sushi, but you should enjoy one another’s company and have a level of trust and rapport.

People really do quit bosses, not companies. How to spot a bad boss? That’s a different column. 


3. Is your company healthy?

Working for a company that’s in a perpetual downward spiral is soul sucking. I’ve been there with media brands and know others in manufacturing and other challenged industries, and living that decline is not worth what it does to your morale. To put it bluntly, companies can’t cut their way to growth, and executives who know nothing other than cutting are toxic. When that starts happening, the best people will leave as soon as possible, and you should be among them. 

🌱 When companies try to cut their way to growth, the best people will leave as soon as possible, and you should be among them. 

My advice? Don't stick around at a company that relies on cutting employee count in an attempt to grow.


4. Is your company’s culture changing from that which first attracted you to it? 

I have gone from the public sector to a privately held entrepreneurial company that went public to an acquisition to a private-equity-held company to my present job. The cultures at each were different and certainly changed over time and particularly with acquisitions. 

We all know serial startup workers. They live for the disorganized chaos of chasing a great idea with 15 other people. If the company gets some success and becomes more structured and hierarchical, these people leave for the next hot mess with a great idea. As long as you like the culture the founders create and can tolerate some chaos, you’ll have lots of opportunities to take on new challenges and responsibilities. 

Big enterprises work hard to make failure unlikely, which can be reassuring. But that ethos means that entrepreneurial success is also unlikely -- letting employees try crazy new things is too risky for big enterprises. That’s why they acquire to diversify. 

If startups are all about risk and big companies are incredibly risk-averse, most firms fall somewhere on that spectrum. Make sure you know where you’re most comfortable and have a match in your employer. And remember: Culture doesn’t change overnight, but it does change. So if you wake up one day and feel stifled, or worse yet underappreciated, it’s time to juice up the resume. Unless you are in very senior position, you will not change the culture of the company – so don’t try. 

🌱 If startups are all about risk and big companies are incredibly risk-averse, most firms fall somewhere on that spectrum. Make sure you know where you’re most comfortable and have a match in your employer.

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5. Is the rest of your life stable enough for a job change? 

All of the above should be modulated if the focus of your life isn’t your job. Are you thinking about having a child, or have a bunch of them already? Do you have a parent who needs care? Is your side gig looking like it could take off if given another year? 

It’s worth periodically weighing the stressors in your life against the challenges of your job. That doesn’t mean you should stay in a bad situation, but it could mean giving a so-so job some time while you get other factors figured out. Early in my career, I left a job, ended a relationship and moved to a new city, all in a month. I don’t recommend that perfect storm. It can seem liberating in the moment, but when liberty comes without a support structure, rebuilding your career and personal life is that much harder because you can’t lean on one while you fix the other.

🌱 It’s worth periodically weighing the stressors in your life against the challenges of your job.

We all know people who seem perfectly happy in their careers at all times. I see them, and I mostly don’t believe them. My bet is that, just like the Facebook friend with a seemingly perfect life, that LinkedIn facade of career perfection covers up plenty of angst, self-doubt and frustration.

Careers have peaks and valleys, just like every other aspect of life. Take what control you can. Meditate, run five miles, talk to your spouse or friend or therapist, or maybe do all of the above. Do whatever it takes to be mindful, balanced and deliberate. Careers are malleable, and you should be the one doing the shaping.